Review

Recent Advances in Cross-Dehydrogenative-Coupling Reactions Using Molecular Oxygen as the Sole Oxidant

  • Weihui Zhuang ,
  • Xiaofeng Zhang ,
  • Qiufeng Huang
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  • a College of Chemistry & Materials Science, Fujian Normal University, Fuzhou 350007
    b Key Laboratory of Polymer Materials of Fujian Province, Fuzhou350007

Received date: 2020-07-02

  Revised date: 2020-08-23

  Online published: 2020-10-28

Supported by

the National Natural Science Foundation of China(21872028); the Foundation of Fujian Educational Committee(JZ160424); the Fujian Province University Fund for New Century Excellent Talents()

Abstract

Cross-dehydrogenative-coupling (CDC) reactions have emerged as one of the most efficient and straightforward methods for the formation of C—C bonds or C-heteroatom bonds. However, most CDC reactions require hazardous and stoichiometric oxidants, such as PhI(OAc)2, benzoquinone, copper(II) salts, organic peroxide acid and silver(I) salts. A green and environmentary benign approach is using molecular oxygen (O2) as oxidant in the reactions, which usually form water as by-product. According to the classification of catalysts, the research progress of cross dehydrogenation coupling reaction with oxygen as the only oxidant is reviewed.

Cite this article

Weihui Zhuang , Xiaofeng Zhang , Qiufeng Huang . Recent Advances in Cross-Dehydrogenative-Coupling Reactions Using Molecular Oxygen as the Sole Oxidant[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 529 -542 . DOI: 10.6023/cjoc202007007

References

[1]
(a) Chen Z.; Wang B.; Zhang J.; Yu W.; Liu Z.; Zhang Y. Org. Chem. Front. 2015, 2, 1107.
[1]
(b) Yang L.; Huang H. Chem. Rev. 2015, 115, 3468.
[1]
(c) He J.; Wasa M.; Chan K. S. L.; Shao Q.; Yu J.-Q. Chem. Rev. 2017, 117, 8754.
[1]
(d) Murakami K.; Yamada S.; Kaneda T.; Itami K. Chem. Rev. 2017, 117, 9302.
[1]
(e) Newton C.G.; Wang S.-G.; Oliveira C.C.; Cramer N. C hem. Rev. 2017, 117, 8908.
[1]
(f) Karimov R.R.; Hartwig J.F. Angew. Chem. Int. Ed. 2018, 57, 4234.
[1]
(g) Zheng L.; Hua R. Chem. Rec. 2018, 18, 556.
[1]
(h) Niu B.; Yang K.; Lawrence B.; Ge H. ChemSusChem 2019, 12, 2955.
[2]
(a) Liu C.; Yuan J.; Gao M.; Tang S.; Li W.; Shi R.; Lei A. Chem. Rev. 2015, 115, 12138.
[2]
(b) Kim H.; Chang S. ACS Catal. 2016, 6, 2341.
[2]
(c) Henry M.C.; Mostafa M. A. B.; Sutherland A. Synthesis 2017, 49, 4586.
[2]
(d) Lakshman M.K.; Vuram P.K. Chem. Sci. 2017, 8, 5845.
[2]
(e) Varun B.V.; Dhineshkumar J.; Bettadapur K.R.; Siddaraju Y.; Alagiri K.; Prabhu K.R. Tetrahedron Lett. 2017, 58, 803.
[2]
(f) Yang Y.; Lan J.; You J. Chem. Rev. 2017, 117, 8787.
[2]
(g) Tang S.; Zeng L.; Lei A. J. Am. Chem. Soc. 2018, 140, 13128.
[2]
(h) Huang C.-Y.; Kang H.; Li J.; Li C.-J. J. Org. Chem. 2019, 84, 12705.
[3]
(a) Campbell A.N.; Stahl S.S. Acc. Chem. Res. 2012, 45, 851.
[3]
(b) Shi Z.; Zhang C.; Tang C.; Jiao N. Chem. Soc. Rev. 2012, 41, 3381.
[3]
(c) McCann S.D.; Stahl S.S. Acc. Chem. Res. 2015, 48, 1756.
[3]
(d) Liang Y.-F.; Jiao N. Acc. Chem. Res. 2017, 50, 1640.
[4]
(a) Chen X.; Engle K.M.; Wang D.-H.; Yu J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094.
[4]
(b) Lyons T.W.; Sanford M.S. Chem. Rev. 2010, 110, 1147.
[4]
(c) He C.; Whitehurst W.G.; Gaunt M.J. Chem 2019, 5, 1031.
[4]
(d) Shao Q.; Wu K.; Zhuang Z.; Qian S.; Yu J.-Q. Acc. Chem. Res. 2020, 53, 833.
[5]
Campbell A.N.; Stahl S.S. Acc. Chem. Res. 2012, 45, 851.
[6]
Wang D.; Weinstein A.B.; White P.B.; Stahl S.S. Chem. Rev. 2017, 118, 2636.
[7]
Zhang Y.-H.; Shi B.-F.; Yu J.-Q. J. Am. Chem. Soc. 2009, 131, 5072.
[8]
Piotrowicz M.; Zakrzewski J. Organometallics 2013, 32, 5709.
[9]
Piotrowicz M.; Zakrzewski J.; Metivier R.; Brosseau A.; Makal A.; Wozniak K. J. Org. Chem. 2015, 80, 2573.
[10]
Liu B.; Jiang H.-Z.; Shi B.-F. J. Org. Chem. 2014, 79, 1521.
[11]
Shi B.-F.; Maugel N.; Zhang Y.-H.; Yu J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
[12]
Engle K.M.; Wang D.-H.; Yu J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169.
[13]
Engle K.M.; Wang D.-H.; Yu J.-Q. J. Am. Chem. Soc. 2010, 132, 14137.
[14]
Cong X.; Tang H.; Wu C.; Zeng X. Organometallics 2013, 32, 6565.
[15]
Huang Q.; Zhang X.; Qiu L.; Wu J.; Xiao H.; Zhang X.; Lin S. Adv. Synth. Catal. 2015, 357, 3753.
[16]
Zhang X.; Su L.; Qiu L.; Fan Z.; Zhang X.; Lin S.; Huang Q. Org. Biomol. Chem. 2017, 15, 3499.
[17]
Pan G.; Wu K.; Deng Z.; Zhang X.; Zhang X.; Lin S.; Huang Q. Chin. J. Org. Chem. 2018, 38, 2076. (in Chinese)
[17]
潘帼帅, 吴孔川, 邓泽颖, 张馨予, 张晓凤, 林深, 黄秋锋, 有机化学, 2018, 38, 2076.).
[18]
(a) Jeffery T. Tetrahedron 1996, 52, 10113.
[18]
(b) Phan N. T. S.; Van Der Sluys M.; Jones C.W. Adv. Synth. Catal. 2006, 348, 609.
[19]
Wei Y.; Deb I.; Yoshikai N. J. Am. Chem. Soc. 2012, 134, 9098.
[20]
Ghosh M.; Naskar A.; Mitra S.; Hajra A. Eur. J. Org. Chem. 2015, 2015, 715.
[21]
Wu Y.-B.; Xie D.; Zang Z.-L.; Zhou C.H.; Cai G.-X. Chem. Commun. 2018, 54, 4437.
[22]
Shan C.; Bai R.; Lan Y. Acta Phys.-Chim. Sin. 2019, 35, 940. (in Chinese)
[22]
单春晖, 白若鹏, 蓝宇, 物理化学学报, 2019, 35, 940.).
[23]
Li H.; Shi Z. Prog. Chem. 2010, 22, 1414. (in Chinese)
[23]
李湖, 施章杰, 化学进展, 2010, 22, 1414.).
[24]
Liegault B.; Lee D.; Huestis M.P.; Stuart D.R.; Fagnou K. J. Org. Chem. 2008, 73, 5022.
[25]
(a) Min M.; Kim Y.; Hong S. Chem. Commun. 2013, 49, 196.
[25]
(b) Kim N.; Min M.; Hong S. Org. Chem. Front. 2015, 2, 1621.
[25]
(c) Mizuta Y.; Yasuda K.; Obora Y. J. Org. Chem. 2013, 78, 6332.
[25]
(d) Lv J.; Liang Y.; He P.; Cai Z.; Liu J.; Huang F. RSC Adv. 2015, 5, 36171.
[26]
(a) Xu Y.-H.; Chok Y.K.; Loh T.-P. Chem. Sci. 2011, 2, 1822.
[26]
(b) Zhou L.; Lu W. Organometallics 2012, 31, 2124.
[26]
(c) Chen W.-L.; Gao Y.-R.; Mao S.; Zhang Y.-L.; Wang Y.-F.; Wang Y.-Q. Org. Lett. 2012, 14, 5920.
[26]
(d) Li N.-N.; Zhang Y.-L.; Mao S.; Gao Y.-R.; Guo D.-D.; Wang Y.-Q. Org. Lett. 2014, 16, 2732.
[26]
(e) Ishida N.; Nakanishi Y.; Moriya T.; Murakami M. Chem. Lett. 2011, 40, 1047.
[26]
(f) Yang D.; Mao S.; Gao Y.-R.; Guo D.-D.; Guo S.-H.; Li B.; Wang Y.-Q. RSC Adv. 2015, 5, 23727.
[27]
Rogers M.M.; Kotov V.; Chatwichien J.; Stahl S.S. Org. Lett. 2007, 9, 4331.
[28]
(a) Yang L.; Zhang G.; Huang H. Adv. Synth. Catal. 2014, 356, 1509.
[28]
(b) Tang J.; Li S.; Liu Z.; Zhao Y.; She Z.; Kadam V.D.; Gao G.; Lan J.; You J. Org. Lett. 2017, 19, 604.
[29]
Feng C.; Loh T.-P. J. Am. Chem. Soc. 2010, 132, 17710.
[30]
Dey A.; Ali M.A.; Jana S.; Samanta S.; Hajra A. Tetrahedron Lett. 2017, 58, 313.
[31]
Kumar K.S.; Meesa S.R.; Naikawadi P.K. Org. Lett. 2018, 20, 6079.
[32]
(a) Ueura K.; Satoh T.; Miura M. Org. Lett. 2007, 9, 1407.
[32]
(b) Colby D.A.; Bergman R.G.; Ellman J.A. Chem. Rev. 2010, 110, 624.
[32]
(c) Patureau F.W.; Joanna W.-D.; Glorius F. Aldrichim. Acta 2012, 45, 31.
[32]
(d) Song G.; Li X. Acc. Chem. Res. 2015, 48, 1007.
[32]
(e) Li S.-S.; Qin L.; Dong L. Org. Biomol. Chem. 2016, 14, 4554.
[32]
(f) Qi X.; Li Y.; Bai R.; Lan Y. Acc. Chem. Res. 2017, 50, 2799.
[32]
(g) Vásquez-Céspedes S.; Wang X.; Glorius F. ACS Catal. 2017, 8, 242.
[32]
(h) Rej S.; Chatani N. Angew. Chem. Int. Ed. 2019, 58, 8304.
[32]
(i) Zhu W.; Gunnoe T.B. Acc. Chem. Res. 2020, 53, 920.
[33]
(a) Zhang G.; Yang L.; Wang Y.; Xie Y.; Huang H. J. Am. Chem. Soc. 2013, 135, 8850.
[33]
(b) Han W.; Zhang G.; Li G.; Huang H. Org. Lett. 2014, 16, 3532.
[33]
(c) Zhang G.; Yu H.; Qin G.; Huang H. Chem. Commun. 2014, 50, 4331.
[34]
Lu Y.; Wang H.-W.; Spangler J.E.; Chen K.; Cui P.-P.; Zhao Y.; Sun W.-Y.; Yu J.-Q. Chem. Sci. 2015, 6, 1923.
[35]
Jiang Q.; Zhu C.; Zhao H.; Su W. Chem.- Asian J. 2016, 11, 356.
[36]
Jambu S.; Sivasakthikumaran R.; Jeganmohan M. Org. Lett. 2019, 21, 1320.
[37]
(a) Arockiam P.B.; Bruneau C.; Dixneuf P.H. Chem. Rev. 2012, 112, 5879.
[37]
(b) Ackermann L.; Vicente R. Top. Curr. Chem. 2010, 292, 211.
[37]
(c) Ackermann L. Acc. Chem. Res. 2014, 47, 281.
[37]
(d) Ruiz S.; Villuendas P.; Urriolabeitia E.P. Tetrahedron Lett. 2016, 57, 3413.
[37]
(e) Nareddy P.; Jordan F.; Szostak M. ACS Catal. 2017, 7, 5721.
[37]
(f) Khan F.F.; Sinha S.K.; Lahiri G.K.; Maiti D. Chem.-Asian J. 2018, 13, 2243.
[37]
(g) Shan C.; Zhu L.; Qu L.-B.; Bai R.; Lan Y. Chem. Soc. Rev. 2018, 47, 7552.
[38]
Bechtoldt A.; Tirler C.; Raghuvanshi K.; Warratz S.; Kornhaass C.; Ackermann L. Angew. Chem., Int. Ed. 2016, 55, 264.
[39]
Bechtoldt A.; Baumert M.E.; Vaccaro L.; Ackermann L. Green Chem. 2018, 20, 398.
[40]
Li X.; Hu X.; Liu Z.; Yang J.; Mei B.; Dong Y.; Liu G. J. Org. Chem. 2020, 85, 5916.
[41]
Hayashi H.; Ueno T.; Kim C.; Uchida T. Org. Lett. 2020, 22, 1469.
[42]
(a) Gandeepan P.; Muller T.; Zell D.; Cera G.; Warratz S.; Ackermann L. Chem. Rev. 2019, 119, 2192.
[42]
(b) Loginov D.A.; Shul'pina L.S.; Muratov D.V.; Shul'pin G.B. Coord. Chem. Rev. 2019, 387, 1.
[42]
(c) Loup J.; Dhawa U.; Pesciaioli F.; Wencel-Delord J.; Ackermann L. Angew. Chem. Int. Ed. 2019, 58, 12803.
[42]
(d) Ackermann L. Acc. Chem. Res. 2020, 53, 84.
[43]
Egami H.; Katsuki T. J. Am. Chem. Soc. 2009, 131, 6082.
[44]
Egami H.; Matsumoto K.; Oguma T.; Kunisu T.; Katsuki T. J. Am. Chem. Soc. 2010, 132, 13633.
[45]
Niu T.; Zhang Y. Tetrahedron Lett. 2010, 51, 6847.
[46]
Fritsche R.F.; Theumer G.; Kataeva O.; Kn?lker H.J. Angew. Chem., Int. Ed. 2017, 56, 549.
[47]
Purtsas A.; Kataeva O.; Kn?lker H.J. Chem.-Eur. J. 2019, 25, 13759.
[48]
Huang T.; Liu X.; Lang J.; Xu J.; Lin L.; Feng X. ACS Catal. 2017, 7, 5654.
[49]
Huang X.; Chen Y.; Zhen S.; Song L.; Gao M.; Zhang P.; Li H.; Yuan B.; Yang G. J. Org. Chem. 2018, 83, 7331.
[50]
Reiss H.; Shalit H.; Vershinin V.; More N.Y.; Forckosh H.; Pappo D. J. Org. Chem. 2019, 84, 7950.
[51]
Liu Y.-H.; Liu Y.-J.; Yan S.-Y.; Shi B.-F. Chem. Commun. 2015, 51, 11650.
[52]
Nishino M.; Hirano K.; Satoh T.; Miura M. Angew. Chem., Int. Ed. 2012, 51, 6993.
[53]
Zhang G.; Ma Y.; Wang S.; Zhang Y.; Wang R. J. Am. Chem. Soc. 2012, 134, 12334.
[54]
Fraser J.; Wilson L.J.; Blundell R.K.; Hayes C.J. Chem. Commun. 2013, 49, 8919.
[55]
Wang C.; Yang Y.; Qin D.; He Z.; You J. J. Org. Chem. 2015, 80, 8424.
[56]
Ahmad A.; Dutta H.S.; Khan B.; Kant R.; Koley D. Adv. Synth. Catal. 2018, 360, 1644.
[57]
Santoro S.; Kozhushkov S.I.; Ackermann L.; Vaccaro L. Green Chem. 2016, 18, 3471.
[58]
Matsushita M.; Kamata K.; Yamaguchi K.; Mizuno N. J. Am. Chem. Soc. 2005, 127, 6632.
[59]
Jin X.; Yamaguchi K.; Mizuno N. Chem. Commun. 2012, 48, 4974.
[60]
Ishida T.; Aikawa S.; Mise Y.; Akebi R.; Hamasaki A.; Honma T.; Ohashi H.; Tsuji T.; Yamamoto Y.; Miyasaka M.; Yokoyama T.; Tokunaga M. ChemSusChem 2015, 8, 695.
[61]
Dutta B.; Biswas S.; Sharma V.; Savage N.O.; Alpay S.P.; Suib S.L. Angew. Chem., Int. Ed. 2016, 55, 2171.
[62]
Singh H.; Pal P.; Sen C.; Panda A.B.; Ghosh S.C. Asian J. Org. Chem. 2017, 6, 702.
[63]
Yang W.; Wei L.; Yan T.; Cai M. Catal. Sci. Technol. 2017, 7, 1744.
[64]
Yatabe T.; Jin X.; Mizuno N.; Yamaguchi K. ACS Catal. 2018, 8, 4969.
[65]
Matsumoto K.; Takeda S.; Hirokane T.; Yoshida M. Org. Lett. 2019, 21, 7279.
[66]
Bering L.; Vogt M.; Paulussen F.M.; Antonchick A.P. Org. Lett. 2018, 20, 4077.
[67]
Saha S.; Banerjee A.; Maji M.S. Org. Lett. 2018, 20, 6920.
[68]
Chen Q.; Yu G.; Wang X.; Ou Y.; Huo Y. Green Chem. 2019, 21, 798.
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